Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3946 - 3951
Published: Jan. 1, 2024
A copper-catalyzed yne-propargylic substitution using amines as nucleophiles has been achieved for the first time, affording a variety of having diyne moieties, which are important pharmacophores in many bioactive molecules.
Language: Английский
Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 11, P. 100082 - 100082
Published: July 3, 2024
Language: Английский
Citations
10
Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(34), P. 15779 - 15785
Published: Aug. 17, 2022
Distinct regio- and enantioselectivity control in copper-catalyzed vinylogous bisvinylogous propargylic substitution has been accomplished by using a novel chiral N,N,P ligand. The developed method provides an efficient selective approach to array of highly enantioenriched alkynyl unsaturated carbonyl compounds. Salient features include excellent functional group tolerance broad substrate scope. synthetic utility the is further demonstrated gram-scale synthesis application range transformations including enantioselective unique challenging
Language: Английский
Citations
38
Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(43), P. 19932 - 19941
Published: Oct. 21, 2022
Searching for efficient strategies to access structurally novel aminoindolines is of great significance drug discovery. However, catalytic asymmetric de novo construction aminoindoline scaffolds with functionality primed diversification still remains elusive. Here, we report a Cu-catalyzed cyclization ethynyl benzoxazinones amines, producing chiral 3-aminoindolines in good yield and high enantioselectivity (up 97% 98:2 er). Moreover, radical-mediated sulfonyl migration these products was unexpectedly found, further affording new bearing alkenyl groups retained enantiopurity 84% Bioactivity evaluations indicate that show notable antitumor activities chirality proven have significant impact on their activity.
Language: Английский
Citations
31
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(3), P. 690 - 695
Published: Dec. 5, 2023
A reliable protocol for asymmetric Cu-catalyzed alkynylallylic dimethylamination is described with the discovery of tetramethyldiaminomethane as a new, stable and convenient surrogate dimethylamine nucleophile.
Language: Английский
Citations
18
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(15), P. 11646 - 11656
Published: July 22, 2024
Language: Английский
Citations
6
Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(51)
Published: Oct. 27, 2022
In contrast to previous approaches chiral α-aryl carboxylic acids that based on reactions using hazardous gases, pressurized setup and mostly noble metal catalysts, in this work, a nickel-catalyzed general, efficient highly enantioselective carboxylation reaction of racemic benzylic (pseudo)halides under mild conditions atmospheric CO2 has been developed. A unique 2,2'-bipyridine ligand named Me-SBpy featuring compact polycyclic skeleton enabled both high reactivity stereoselectivity. The utility method demonstrated by synthesis various (30 examples, up 95 % yield 99 : 1 er), including profen family anti-inflammatory drugs transformations the as key intermediates. Based mechanistic experimental results, plausible catalytic cycle involving Ni-complex/radical equilibrium Lewis acid-assisted activation proposed.
Language: Английский
Citations
28
Organic Letters, Journal Year: 2022, Volume and Issue: 24(28), P. 5120 - 5125
Published: July 12, 2022
A copper-catalyzed decarboxylative cascade cyclization of propargylic cyclic carbonates/carbamates with pyridinium 1,4-zwitterionic thiolates is developed. range fused polyheterocyclic compounds are obtained in moderate to good yields excellent diastereoselectivities. Of particular note that four new bonds (two C-C, one C-O/N, C-S) and stereocenters could be efficiently embedded into the tetracyclic scaffolds a single step.
Language: Английский
Citations
27
Organic Letters, Journal Year: 2022, Volume and Issue: 24(41), P. 7671 - 7676
Published: Oct. 13, 2022
Enantioselective construction of vicinal tetrasubstituted carbon stereocenters is a formidable challenge in organic synthesis. A copper-catalyzed asymmetric decarboxylative propargylic substitution with 3-amino oxindoles as trisubstituted nucleophiles and cyclic carbonates tertiary electrophiles was developed. range 3-amino-3,3′-disubstituted bearing quaternary-tetrasubstituted were obtained high yields good to excellent stereoselectivities (up 98% yield, >20:1 dr, 98.5:1.5 er).
Language: Английский
Citations
23
Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(22), P. 3097 - 3114
Published: June 20, 2023
Comprehensive Summary Knowledge of asymmetric catalytic reaction mechanism is very important for rational design and synthesis new chiral catalysts or systems with high activity stereoselectivity. The studies nonlinear effect have attracted wide attentions as a simple practical mechanistic tool to probe complex reactions. This review documents the application study effects on how reveal in reactions that were catalyzed by first‐row transition‐metals last decade gives brief discussion different models effect.
Language: Английский
Citations
14
Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110114 - 110114
Published: June 1, 2024
Language: Английский
Citations
5